First Timer
by SuperUkeJet
Summary: Doflamingo has just found a young boy hanging out near the clubs in downtown Dressrosa. He's young, cute, and a perfect person to pick up for some fun for the night. He's sure to make it an unforgettable time for the boy's first time. WARNINGS: Yaoi, Lemons, Toys, Language.


**Hey guys! Here's another requested story that someone asked me to do**

 **First Timer (Requested by: MissYuki15)**

 **Doflamingo has just found a young boy hanging out near the clubs in downtown Dressrosa. He's young, cute, and a perfect person to pick up for some fun for the night. He's sure to make it an unforgettable time for the boy's first time.**

 **Pairing: Doflamingo x Luffy**

 **WARNINGS: Yaoi, Lemon, Language, Toys**

 **Disclaimer: One Piece is not mine, it's Eiichiro Oda's**

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 _First Timer_

Doflamingo just walked out of his favorite club, The Locker Room Dungeon. It was the best club they had in all of downtown Dressrosa, enough to fulfill all his lust, desires and fantasies whenever he needed it. The sounds of chattering people filled the streets as hundred and hundreds of people walked along the cluster of night clubs. He looked up at the sky, a deep black, with very faint stars that could barely be seen due to all the flashing lights.

He started to make his way through the crowds of people to get back home. However, his eyes came across upon a young boy with some jet black hair, leaning against a light post. He was someone you wouldn't usually see in this part of the town; young, innocent-looking and indeed very handsome, to Doflamingo at least. _Finally! Someone I can have fun with tonight._ He eagerly approached the young boy, leaning himself over him. "Hey there, I haven't seen you around here before."

"Yea… just turned 18…" the young man replied to him.

"So you decided to come here and check out all the guys, huh?" he asked.

He smiled, "I guess so."

"You interested in any of this stuff?"

"Haven't really experimented with stuff, if you know what I mean."

"How about you come home with me tonight, and you can experiment all you want. I might have some stuff that you might really enjoy."

"Sounds like a plan. I don't have anything else to do," he answered as Doflamingo put his arms around the boy, guiding him to his Porsche and driving off.

"So what your name?" Doflamingo asked.

"Luffy,"

"And you said you're 18?"

"Sure am."

"Well, I'm Doflamingo. 23,"

"Do-Do… That's hard to say. Can I just call you Doffy?"

"Seriously?" he replied in shock. "I guess that's fine…"

The drive wasn't too long. Perhaps 10 to 15 minutes of them driving through the busy city streets full of bright lights and chattering people. Soon enough, the car turned into and underground parking lot. The two got up and Doflamingo wrapped his arm around Luffy as they proceeded to walk.

"What are you doing?" Luffy questioned

"Just getting comfortable for tonight, love." He subtly added into the sentence. They approached a glass door and the inside lobby was very bright. All the walls were white; there were red carpets all over the floor, romanesque columns decorated the space, as well as smaller pillars that had pots of blooming flowers placed on top. Large couches also filled the room and there was a large marble reception. _Woah! This is a really rich people place!_ Luffy thought to himself.

They entered the giant elevator, perhaps capable of taking 30 people or so. Doflamingo scanned a key card on the wall of buttons and the elevator proceeded to move. Soon enough, the two arrived at the top and the elevator door opened into a fantastic penthouse. It was nice and spacious. The large windows allowed a 360 degree view of the downtown area. The living room contained the biggest TV Luffy has ever seen as well as a large red couch. The kitchen was no less amazing, furnished with the most expensive and high-quality equipment to meet the man's expensive taste.

"You like it?" Doffy asked.

"It's really nice and big!" Luffy smiled back.

"If you think this is big, you should see the bed and bath." Doffy opened the door to the only bedroom in the house. Luffy followed in behind Doflamingo and he was not lying. The bed was the middle of the room; a large XL King sized bed with red silk bedsheets, gold bedframes and rose petals all around, how cliche. Towards the right, it seemed to be a big open concept bathroom, complete with a jacuzzi, shower, sinks, toilets, which probably had some fancy gadgets if Luffy took a closer look.

Then, Luffy's attention shifted to the left side of the room and boy was he surprised. Doflamingo chuckled as Luffy's mouth dropped to the floor. It was pretty obvious why Doflamingo liked to visit The Locker Room Dungeon. The left side was filled with shelves and shelves of toys. They included dildos of all colours, shapes, and sizes, all sorts of fetish wear like rubber and bondage gear hung on the racks. There was also a bountiful amount of furniture in the "dungeon area" as well.

The tall blonde made his way to the shower. He walked towards the shower just as his shirt fell onto the floor. He unbuckled the pants and pulled them off his long legs, as well as his underwear. His back faced the young boy still standing in the doorway of the large bedroom. Doflamingo's back faced Luffy who is unable to see the goods he came for. After a quick rinse, he wrapped a towel around the waist and made his way over to the dungeon. He faced the boy and asked, "Have you decided to stay? Or do you wanna go?" In an instance, his dropped his towel and revealed that beautiful cock and large balls.

Luffy gulped at the sight and began to undress. It seemed like his feet started to move on their own towards the blonde. His arms reached for his clothing as they were scattered across the floor one by one. "H-How big are you?" Luffy hesitantly asked.

"Why don't you feel for yourself?" He grabbed the small boys hand and guided him towards his own member. Luffy's hands explored the organ. It was long, it was thick and the balls were especially big. "I haven't released in over a week, that's why they're so big," he commented. "Have you tried edging before?"

"Nope," Luffy replied shaking his head, "never heard of that before."

"Have you ever jacked-off?"

"Definitely!"

"So you know how great it feels to cum right?"

"Yup!"

"But when you bring yourself to the point of cumming, and deny yourself from releasing, it feels even better!"

"Really?! That sounds great! I wanna try!"

"Well, if you want to try, I guess we're going to have a very kinky night tonight."

He wrapped his arms around the boy and brought his lips towards the other's. They connected and the two moaned in sync as the tongues fought for dominance. Doflamingo managed to sneak a hand towards Luffy's groin. Luffy's moans got louder as the big hands wrapped around.

"Heh, not a bad size for a guy your age."

The blonde's hands met Luffy's chest as he was pushed onto the bed. Doflamingo gathered many, many objects and toys for them to use for the rest of the night.

"Before we do this… I want to see how good you are with your mouth." He climbed onto the large bed and moved the sheets aside. He spread his legs apart of easy access. Luffy did not hesitate for one bit. His hands moved towards Doflamingo's cock by themselves. He grabbed the long and thick organ as his head went to the pair of balls underneath.

The warmth of his mouth soon engulfed the sack. Luffy licked, sucked and played with them as he pleased. "Yea… that feels great…" the blonde said, putting his hand on Luffy's head. A bead of pre slowly formed on the tip. Luffy quickly picked up on the faint scent and shifted his attention to the head. He gave it a small lick and scooped up the liquid.

"Musky…" he said. He continued onto the glans, the most sensitive part. Luffy's tongue slid all over it, causing a wave of pleasure to move throughout Doflamingo's spine. Luffy went further down, trying his best to fit his massive member into his mouth. He reached his maximum, almost three-quarters down the entire length. Saliva dripped from the mouth and down, coating it in a generous layer. He tried to go down further, but wasn't able to and eventually, came back up.

"You're very talented with your mouth. Are you sure you haven't done this before?" he asked.

"Positive." Luffy wanted to make one more attempt to go all the way. He took a deep breath and quickly inched himself down the shaft. He went five, six, seven, eight and that was all he could go. He inched further to go down nine inches but it hit the back of his throat. His eyes teared up and he came back up right away, panting.

"Fufufu. Sorry I'm so hung." Doflamingo said sarcastically. "Now let's move on, I'm gonna play with you all night so it's gonna be a night you're not gonna forget." He leaned in closer to whisper into Luffy's ear. "I'm not gonna allow you to release for hours and hours…" His face turned a bright pink from embarrassment.

Doflamingo rummaged through his pile of toys and equipment and pulled out two triple-cock rings. He slicked some lube on his own equipment and slipped it right on himself. His member remained extremely stiff, it was twitching and leaking. "Your turn," he said pouring some lube into his hands. "Ready?"

"I guess so…" he replied in a quiet voice. Doflamingo coated Luffy with a generous amount of lube. He was careful to not hurt him, slipping it onto Luffy's member. "Ah, the lube's cold…" Luffy chuckled.

"Heh, but it makes for a great time. See how hard you're getting?" Doflamingo said as he stroked. "I can tell you wanna cum already, but we just started!"

"Urgh, if you keep rubbing me like that, it's gonna be over sooner than you think," he claimed, squirming a little.

"Fine fine, I'll stop… How about we try something else?" Doflamingo asked.

"Like what?"

"Well, I don't want to do anything with this amazing prize…" he teased as he rubbed Luffy's butt. "I'm pretty you've been online looking at… stuff… if you know what I mean."

"Ya, so what?"

"Is there anything you've always wanted to try?"

"Hmmmm…" Luffy thought. "There is one thing… but it seems pretty intense…"

"Intense you say?" Doflamingo said with intrigue.

"Ya… I've always thought electric stim was pretty hot…" Luffy murmured with a blush.

"Electro-play huh? You're pretty kinky for being so young. But if you want to try, I'd be happy to oblige, it's actually one of my favourite things to do. It always gets me aching for release!" he answered. Carefully sifting through his toys, Doflamingo pulled out a small box with a bunch of wires. "Here's the magical box that will make your dreams come true."

He plugged the wires into the box and attached the other sides to Luffy's nipples. "The great thing is that this box can provide us with two outputs so none of us miss the fun! Let's see… let's try intensity at 5 and pulse mode."

With a quick press of a button, Luffy was jolted with quick pulses of electricity. "Holy crap!" He screamed falling onto the bed. "It feels so good!" His body was quivering with excitement; he was drooling out of his mouth, a clear sign of pure ecstasy. He member twitched more and more, leaking thick, creamy precum.

"If I put that on your dick, you would have come within the first second, and it's not even at the setting to make you cum! The highest is 50 and there is literally a climax mode on this thing. But once you learn how to hold it in, it's just amazing." He prepped himself to join Luffy in on the fun. He attached some wires to his sack and his throbbing erection. "For me… intensity 50, edging mode... FUCK!" he yelled as he turned his part on, dropping the device onto the bed. "Shit! You can feel the electricity in my cock!" Without hesitation, he grabbed Luffy's hand and brought it closer to his member.

"Wow, it so hard!" Luffy complimented as he squeezed it. "There's so much precum, it's like a fountain!"

"This… is what… you can do… if you… urgh… train yourself… to hold it in. I've held it... in for... about... an hour... or so. That was... Sunday.."

Luffy was just amazed by what he saw, compared to Doflamingo, his stimulation is nothing. He could smell a strong scent of musk coming from the older blond who hadn't released all week. He couldn't resist the smell and licked it right of the head.

"Oh no…" Doflamingo grunted. "Too… sensitive!" he screamed. Suddenly he shot precum everywhere. It landed on Luffy, himself, all over the bed and even on the floor. "Fuck, that was great." he panted as he turned the machine off. His cock was hard, it was coated in pre still. His balls were sore, turning bluer and bluer as time went by.

"What was that!" Luffy exclaimed at what just happened. "You just shot and you're still rock hard… I always go soft after I release…"

"That was pre, not the actual thing. If you get horny enough, you could shoot it." Doflamingo explained.

"Woah! Lemme try, sounds hot!" the younger said excitedly spreading his legs for Doflamingo. The blond took the younger's sensitive member into his hands, stroked it gently and started to lick all the pre that gathered at the tip. "Egh…" he squealed from pleasure. "I…I…" he panted as Doflamingo licked faster and faster. "I'm… gonna shoot!" he declared and shot loads of pre all over like Doflamingo did. "That was the best thing I've ever felt!"

"Mmm, all the lube's everywhere and now it's all musky…" Doflamingo complimented. "But, I think we should get our reward before we get too horny."

"It's a little late for that… I'm super horny" Luffy laughed.

The blond gently laid Luffy onto his back. He lifted Luffy's legs onto his shoulders and grabbed the bottle of lube once again. He applied lube all over his fingers and circled the younger's entrance.

"It's cold again…" Luffy said.

"Don't worry it's gonna be hot soon enough…"

He tried to push a finger inside, but the tight ring of muscle was clenching too much. he tried a second time, without success.

"Have you've ever played with… this?" Doflamingo curiously asked.

"N-No… never… I'm just a little nervous just cause it's my first time and all…"

"Don't worry, I don't wanna hurt you, but I just need you to breathe and relax." Luffy inhaled deeply and exhaled just as Doflamingo said. "Breathe in…" he said pushing his index in all the way, "and back out… See, now I'm inside." He wiggled his finger to loosen up the insides. He inserted a second finger and began to spread the hole open. He scissored the insides to loosen them enough.

"It feels funny to have something up there… but it also feels good…" Luffy whispered.

Grabbing a condom from the dresser, he ripped the packet open and doused it in lube. He slid it on his aching organ and stroked a few times to spread the lube,

Doflamingo aligned himself with Luffy. "I'm going in…" Luffy gave him a nodded. Both of them were flushed with pink, the room was heating up even more now and musk filled the air from their previous ordeal. He pushed inside, earning a small whimper from Luffy. He slid in gently to make sure he wasn't hurting the boy. "Fucking hell! You're so tight; you weren't kidding when you said you haven't played with yourself!"

Luffy didn't even what he said; he was focusing on what was inside of him. "I can feel you throbbing inside of me… it's so hot…" he admitted.

'Is it okay for me to move now?"

"Just wait a little bit…" The caverns inside Luffy were squeezing Doflamingo's cock, encasing in intense warmth. Luffy was trying to get adjusted to the foreign feeling. "Okay, I think I'm ready… You can move now."

With gentleness, the blonde started to pull out and back it. Luffy let out a gasp every time he re-entered. "It soo good ~" he blurted.

"And you feel really good too, fu fu fu" Over time, Doflamingo increased his speed and power. He thrust and thrust into Luffy, filling the room with the sound of skin slapping together. Both of their balls grew bigger, aching to shoot their loads.

"Eyaaa!" Luffy screamed as Doflamingo hit his special spot.

"Looks like I've finally found it! It's your sweet spot." He purposely angled himself to hit it every time.

"Argh! It's so good!" Luffy yelled. "Hit it more! More!" he begged.

"Whatever you wish!" Doflamingo replied. "But don't complain when you can't walk tomorrow!" This continued on for about an hour, still thrusting, still moaning, and still no release. "You last a really long time for being a virgin!"

"Thanks, but I think I'm at my limit, I can't hold it in much longer…" he growled trying to stop himself from releasing.

"Just cum for me, Luffy…" Doflamingo whispered.

"Cumming!" the younger boy declared without second thoughts as his back arched. "Aaah!" he screamed as his member pumped out all the sticky white goodness all over their sweaty, muscled bodies. He fell back onto the bed, panting.

"I guess it time for me to finish too…" Doflamingo panted out. He quickly pulled himself out of Luffy and ripped the condom right off. He started to stroke his cock at lightning speed. Pre dripped and drooled all over Luffy, he knew that Doffy was close. "Urgh! Fuck yea! Take my week load!" Doflamingo declared as he released all over Luffy, covering him nearly everywhere.

"It's so hot and sticky..." Luffy panted out.

"How was that for your first time out?" the older asked as he flopped over beside Luffy.

"Hot… It was great…" Luffy replied, giving Doflamingo a kiss. "For my first time, it was pretty kinky."

"Then, I can't wait to go at it again," he smiled.

THE END

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 **Thanks for reading!**

 **Please R &R! Got a request? Drop it off in my inbox!**

 **~SuperUkeJet**


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